The Most Unique Challenges To Dating In Every Age Range

Everyone struggles with dating, no matter what age.

man and woman on coffee date Jacob Lund / Shutterstock

"Dating" may be a catch-all for putting yourself out there in the quest for love. You meet someone new, go out for coffee or dinner, get swept up in all the feel-good, babysit the phone for the next call or text.

But, for all that makes dating same-ol’-same-ol’, regardless of who-what-where, it actually poses some unique challenges for different age groups.

When you really stop to think about it, it’s almost a cosmic wonder that people end up together. Considering all the differences between — their upbringings, values, and interests — it seems as if the odds would be against them.


And the progressive decline in marriage rates in this millennium inspires more questions than answers. 

Why is finding true love so difficult? Are people just waiting longer to marry? Are couples choosing alternatives to marriage? 

Are there socioeconomic reasons for the decline? Are certain age groups marrying more or less than other age groups? Are people looking for different things than they used to look for when it comes to love?

How much does age have to do with it? Is love really worth it?

And yet, in spite of statistics and skepticism, love is still the hottest pursuit. Always has been. Probably always will be.


But it’s still a good idea to have some informed arrows in your quiver.

RELATED: What It Really Takes To Find Love And Be In A Perfect Relationship

Here are some of the biggest and most unique dating problems at every age range.

Challenges of dating in your 20s.

It’s a shame that the perks of youth get showered on the young. They’re healthy, aches-and-pains-free, energetic, and open to the differences and discoveries that make life interesting and the world a hopeful place to inhabit. 

They’re also relatively inexperienced at adult life, often still in or just getting out of college. They’re standing at the starting blocks of life, waiting for the countdown of ready-set-go. 


Ironically, over 50% of young adults ages 18-29 still live at home with at least one parent. This can be a bit awkward when it comes to serious dating or working on an exclusive, long-term relationship. 

But, when you consider factors like the cost of living, limited finances, job searches, student debt, and the COVID pandemic, the growing trend makes sense. 

This is also a time in life when most young adults are "me"-focused.

"Where do I want to go? What do I want to do? What sounds like fun for the weekend?"

Compared to older singles, Millennials/Gen Y-ers/Gen Z-ers are tech-savvy. Dating apps aren’t self-shaming topics for closet conversations. They’re as routine as gaming and downloading music. 


Tech is something they grew up with. And, for singles in their 20s, it plays a dominant role in their lives, often to the exclusion of meeting people and developing relationships IRL. 

The very nature of internet dating can lead to game-playing between people — ghosting, waiting to call, slacking on healthy communication. 

Finally, these years of starting careers and pursuing personal interests can highlight what often becomes a source of tension between men and women. 

Even women who want to travel and pursue their careers in their 20s are aware of their biological clocks.

For those who want to have children one day, the choices they make in the present have relevance down the road. 


Many men, on the other hand, stretch out the "me" period without worrying about the timing of children. Not a big deal right now, perhaps.

But, when the 20s become the 30s and beyond, that mindset will show its hand.

Dating problems in your 30s.

The irony of dating in your 30s is that you’re still youthful, with the majority of your life ahead of you. 

And yet, if you’re not in a committed relationship by this point, you’ll notice a shrinking candidate pool. 

Many of your friends may already be married (and, as with most young women, you may have built up quite a collection of bridesmaid dresses.) 

College (even high school) is a bit of a utopia when it comes to dating. You are literally immersed in a pool of similarly aged singles. And your responsibilities pretty much revolve around you — your studies, your friends, your activities, your interests. 


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You may have a job, but you’re not waist-deep in financial responsibility. 

And you have constant opportunities to socialize — parties, dances, and sporting events. 

By the time you hit your 30s though, you may have become established in a career. You may be locked into living in a certain city or even having to travel regularly for work. 

That "utopia" of stud, play, and socialize has given way to increasing responsibility. You now have a view into the next decade and the approach of middle-age. 

What do you need to do to prepare? How do you need to spend, save, and invest your money? 


Thirty-somethings usually have enough relationship experience to also have some "baggage." Perhaps, you have had a painful breakup or two. Perhaps, your 20s were a cautionary tale. 

Whatever you bring into your 30s, there has probably been a loss of ease and innocence. 

The topic of children also becomes "the elephant in the room."

Interestingly, as women age (and as they have children), their desire to have more children wanes. 

The opposite is true for men. Yes, guys get baby fever, too! 

For marriage-minded people with hopes of having a family, this is the time to be honest about what you want and to make decisions accordingly. 

Challenges of dating in your 40s and beyond.

Dating problems later in life can be summed up in four words: everything’s more complicated now. 


On one hand, middle-age usually heralds greater self-awareness, maturity, and wisdom. It can be an incredibly liberating time for people who have been locked into their careers and raising children. 

However, if you find yourself back in the dating pool after 40, chances are this isn’t your first go-round, and that can be incredibly unsettling. 

It’s rare for a single in this age bracket to re-enter dating without a previous long-term relationship or marriage.

That means either a painful breakup, divorce, or widowhood, none of which is easy, and all of which come with grief and adjustment. 

Many people in this situation are afraid to be alone, so they jump the gun on dating.


They put a profile on dating apps before being completely divorced. Or they ignore their grief in order not to face it. Or they fail to consider their own role in their past marriage and divorce, dragging their victimhood into their dating life. 

If they've been married for decades, they may not recognize the current approach to modern dating. Technology and internet dating may seem awkward, unnatural, and frustrating

There's also that hot little topic of sex.

Out of practice? Stuck in your old-marriage approach to intimacy? Age-related physical problems with sex? Just not feeling the urge anymore? Need a trip to the medicine cabinet before going to the bedroom? 


These are all normal experiences as people age, and they can certainly pose a challenge to a new dating life. 

Another challenge to dating after 40 is the awkward topic of age-difference expectations. 

While men aren’t the only ones who reach down in the age pool, they are more likely to forego their contemporaries for younger models.

Some need the boost to their egos. Some don’t want any reminder of their marriages. Some still want to have children. 


And some simply look in the mirror and see themselves as the youthful Casanovas they once were. 

Whatever their reasons, their insistence on fishing in a younger pond can pose a frustrating, deflating challenge to women trying to date after 40. 

Forty-plus women end up "competing" with women often young enough to be their daughters. And they often face the double-standard of being “too old” for men who are older than they are. 

Instead of initial conversations about having children, dating and considering marriage after 40 may be more about raising children and blending families. 

Single parents of young children have to think about every aspect of dating problems from a complex perspective.

When do you make introductions? Bring a date home? Spend the night? 


What if you both have children? What if some are grown and some are still at home? 

Dating later in life, despite its unique benefits, is simply more complicated. 

Everyone has "baggage" and history. You’ll never have that “growing up together” kind of relationship, even if you grow old together.

Dating has its unique challenges, to be sure. And some, as we’ve seen, follow a general pattern related to age.

But, then, isn’t that the way life works in general, regardless of dating? 

We give up the ease of youth for the acceptance and wisdom that come with age. 

We look for different things for and from ourselves, and from our relationships.


And we find that life has a funny, redeeming way of balancing the challenges with benefits.

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Amy Schoen is a D.C.-based national expert in dating and relationship life coaching with a proven methodology to access true love through her Meet Your Mate Strategy Sessions